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  • C04B38/00—Porous mortars, concrete, artificial stone or ceramic ware; Preparation thereof
  • C04B38/06—Porous mortars, concrete, artificial stone or ceramic ware; Preparation thereof by burning-out added substances by burning natural expanding materials or by sublimating or melting out added substances
  • C04B38/063—Preparing or treating the raw materials individually or as batches
  • C04B38/0635—Compounding ingredients
  • C04B38/0645—Burnable, meltable, sublimable materials
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  • B32B15/00—Layered products comprising a layer of metal
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  • B32B15/00—Layered products comprising a layer of metal
  • B32B15/20—Layered products comprising a layer of metal comprising aluminium or copper
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  • B32B5/00—Layered products characterised by the non- homogeneity or physical structure, i.e. comprising a fibrous, filamentary, particulate or foam layer; Layered products characterised by having a layer differing constitutionally or physically in different parts
  • B32B5/16—Layered products characterised by the non- homogeneity or physical structure, i.e. comprising a fibrous, filamentary, particulate or foam layer; Layered products characterised by having a layer differing constitutionally or physically in different parts characterised by features of a layer formed of particles, e.g. chips, powder or granules
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  • C04B35/00—Shaped ceramic products characterised by their composition; Ceramics compositions; Processing powders of inorganic compounds preparatory to the manufacturing of ceramic products
  • C04B35/515—Shaped ceramic products characterised by their composition; Ceramics compositions; Processing powders of inorganic compounds preparatory to the manufacturing of ceramic products based on non-oxide ceramics
  • C04B35/58—Shaped ceramic products characterised by their composition; Ceramics compositions; Processing powders of inorganic compounds preparatory to the manufacturing of ceramic products based on non-oxide ceramics based on borides, nitrides, i.e. nitrides, oxynitrides, carbonitrides or oxycarbonitrides or silicides
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  • C04B35/58—Shaped ceramic products characterised by their composition; Ceramics compositions; Processing powders of inorganic compounds preparatory to the manufacturing of ceramic products based on non-oxide ceramics based on borides, nitrides, i.e. nitrides, oxynitrides, carbonitrides or oxycarbonitrides or silicides
  • C04B35/583—Shaped ceramic products characterised by their composition; Ceramics compositions; Processing powders of inorganic compounds preparatory to the manufacturing of ceramic products based on non-oxide ceramics based on borides, nitrides, i.e. nitrides, oxynitrides, carbonitrides or oxycarbonitrides or silicides based on boron nitride
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  • C04B41/00—After-treatment of mortars, concrete, artificial stone or ceramics; Treatment of natural stone
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  • C04B41/00—After-treatment of mortars, concrete, artificial stone or ceramics; Treatment of natural stone
  • C04B41/45—Coating or impregnating, e.g. injection in masonry, partial coating of green or fired ceramics, organic coating compositions for adhering together two concrete elements
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  • C04B41/45—Coating or impregnating, e.g. injection in masonry, partial coating of green or fired ceramics, organic coating compositions for adhering together two concrete elements
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  • C04B41/45—Coating or impregnating, e.g. injection in masonry, partial coating of green or fired ceramics, organic coating compositions for adhering together two concrete elements
  • C04B41/46—Coating or impregnating, e.g. injection in masonry, partial coating of green or fired ceramics, organic coating compositions for adhering together two concrete elements with organic materials
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  • C04B41/80—After-treatment of mortars, concrete, artificial stone or ceramics; Treatment of natural stone of only ceramics
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  • C04B41/81—Coating or impregnation
  • C04B41/89—Coating or impregnation for obtaining at least two superposed coatings having different compositions
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  • B32B2260/00—Layered product comprising an impregnated, embedded, or bonded layer wherein the layer comprises an impregnation, embedding, or binder material
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  • B32B2307/00—Properties of the layers or laminate
  • B32B2307/20—Properties of the layers or laminate having particular electrical or magnetic properties, e.g. piezoelectric
  • B32B2307/206—Insulating
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  • C04B2235/02—Composition of constituents of the starting material or of secondary phases of the final product
  • C04B2235/30—Constituents and secondary phases not being of a fibrous nature
  • C04B2235/32—Metal oxides, mixed metal oxides, or oxide-forming salts thereof, e.g. carbonates, nitrates, (oxy)hydroxides, chlorides
  • C04B2235/3205—Alkaline earth oxides or oxide forming salts thereof, e.g. beryllium oxide
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  • C04B2235/34—Non-metal oxides, non-metal mixed oxides, or salts thereof that form the non-metal oxides upon heating, e.g. carbonates, nitrates, (oxy)hydroxides, chlorides
  • C04B2235/3409—Boron oxide, borates, boric acids, or oxide forming salts thereof, e.g. borax
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Definitions

• the present disclosure relates to a composite, a method for producing a composite, a laminate, and a method for producing a laminate.
• EP 3 428 223A relates to a ceramic-resin composite body comprising a sintered body having a monolithic structure in which three-dimensionally continuous non-oxide ceramic primary particles have a specific average major diameter and aspect ratio.
• the sintered body is impregnated with a thermosetting resin composition having a minimum exothermic onset temperature of 180 °C, a specific curing rate and number average molecular weight.
• Patent Literature 1 International Publication WO 2014/196496
• a composite including a nitride sintered body having a porous structure and a semi-cured product of a heat-curable composition impregnated into the nitride sintered body, wherein a dielectric breakdown voltage obtainable after disposing the composite between adherends, heating and pressurizing the composite for 5 minutes under the conditions of 200°C and 10 MPa, and further heating the composite for 2 hours under the conditions of 200°C and atmospheric pressure, is greater than 5 kV.
• the semi-cured product has a structural unit derived from a cyanate group, a structural unit derived from a bismaleimide group, and a structural unit derived from an epoxy group. The content of the semi-cured product is 20% to 70% by volume.
• the composite includes a semi-cured product of a heat-curable composition, the composite has excellent adhesiveness to an adherend. Since the composite has a specific dielectric breakdown voltage in adhesion under the above-mentioned conditions, the composite has excellent insulation properties after adhesion to an adherend.
• the semi-cured product has a structural unit derived from a cyanate group, a structural unit derived from a bismaleimide group, and a structural unit derived from an epoxy group.
• the semi-cured product contains the specific structural units, the insulation properties and adhesiveness of the composite to an adherend can be enhanced.
• the semi-cured product may contain at least one curing agent selected from the group consisting of a phosphine-based curing agent and an imidazole-based curing agent.
• a curing agent selected from the group consisting of a phosphine-based curing agent and an imidazole-based curing agent.
• the content of the semi-cured product is 20% to 70% by volume.
• the content of the semi-cured product upon being adhered to an adherend, the semi-cured product may be caused to be appropriately present at the interface with the adherend, and the adhesiveness of the composite to the adherend may be enhanced.
• the composite when the content of the semi-cured product is in the above-described range, the composite may also have superior insulation properties after adhesion to the adherend.
• a method for producing a composite having a nitride sintered body having a porous structure and a semi-cured product of a heat-curable composition impregnated into the nitride sintered body including impregnating a nitride sintered body having a porous structure with a heat-curable composition; and heating the heat-curable composition to a heating temperature of 80°C to 130°C to semi-cure the heat-curable composition, wherein the impregnating is a step of impregnating the nitride sintered body with the heat-curable composition by setting the temperature of the heat-curable composition to be higher than the heating temperature and lower than or equal to (the heating temperature + 20°C), and the heat-curable composition contains a compound having a cyanate group, a compound having a bismaleimide group, and a compound having an epoxy group; and at least one curing agent selected from the group consisting of a pho
• the method for producing a composite has impregnating a nitride sintered body having a porous structure with a heat-curable composition, and semi-curing the heat-curable composition, and a composite may be easily produced by impregnating a nitride sintered body with a heat-curable composition and then curing the heat-curable composition. Furthermore, since the resulting composite includes a semi-cured product of the heat-curable composition, the composite has excellent adhesiveness to an adherend. Since the composite has a specific dielectric breakdown voltage in adhesion under the above-mentioned conditions, the composite has excellent insulation properties after adhesion to an adherend.
• a laminate including a first metal base material; an interlayer; and a second metal base material in this order, wherein the first metal base material and the second metal base material are adhered by the interlayer, and the interlayer is a cured product of the composite.
• the laminate is such that a cured product of the composite is the interlayer, the laminate has excellent adhesiveness between the first metal base material and the second metal base material and has excellent insulation properties after adhesion.
• a method for producing a laminate including a first metal base material, an interlayer, and a second metal base material in this order, the method including disposing the first metal base material, the above-mentioned composite, and the second metal base material in this order, heating and pressurizing the assembly to cure the composite, and forming the interlayer.
• a composite having excellent adhesiveness to an adherend and excellent insulation properties after adhesion to the adherend, and a method for producing the composite may be provided.
• An embodiment of the composite is a composite including a nitride sintered body having a porous structure; and a semi-cured product of a heat-curable composition impregnated into the nitride sintered body.
• the composite is such that the dielectric breakdown voltage obtainable after disposing the composite between adherends, heating and pressurizing the composite for 5 minutes under the conditions of 200°C and 10 MPa, and further heating the composite for 2 hours under the conditions of 200°C and atmospheric pressure, is greater than 5 kV.
• stage B state means a state in which a material may be further cured by a subsequent curing treatment.
• a material that is in a semi-cured state may also be utilized and adhered to an adherend by temporarily pressure-bonding the material to the adherend and then heating the material.
• the semi-cured product is in a semi-cured state and may be brought to a "completely cured" (also referred to as stage C) state by being further subjected to a curing treatment. Whether a semi-cured product in a composite is in a semi-cured state that may be further cured may be checked by, for example, using a differential scanning calorimeter.
• the composite includes the semi-cured product of a heat-curable composition impregnated into a nitride sintered body, the composite is capable of adhering to an adherend. Since the composite includes a nitride sintered body, and the pores present in the nitride sintered body are filled with the above-mentioned semi-cured product of a heat-curable composition, the composite has a relatively high dielectric breakdown voltage after adhesion to an adherend and excellent insulation properties. Furthermore, since the composite includes a nitride sintered body, the composite also has a relatively low thermal resistance and excellent thermal conductivity.
• the composite of the present embodiment is useful as an adhesive member which is required to have thermal conductivity and insulation properties (for example, an adhesive sheet and the like). Specifically, the composite of the present embodiment may be used as an adhesive member that adheres a metal circuit board and other layers in a power module structure, an LED light-emitting device, and the like.
• the shape of the composite may be, for example, a block shape, a sheet shape, and the like.
• the thickness of the composite may be, for example, 0.1 mm or more, 0.2 mm or more, or 0.3 mm or more.
• the composite may maintain insulation properties even when used for use applications where high voltage is applied.
• the thickness of the composite may be, for example, 1.0 mm or less, 0.7 mm or less, or 0.4 mm or less.
• the thermal resistance may be made smaller.
• the nitride sintered body having a porous structure may be a product obtained when primary particles of a nitride are sintered together.
• porous structure means a structure having a plurality of fine holes (hereinafter, also referred to as pores) and includes a structure in which at least a portion of the pores are connected to form continuous pores.
• the average pore size of the pores may be, for example, 7 ⁇ m or less, 6 ⁇ m or less, or 5 ⁇ m or less. When the average pore size is in the above-described range, the thermal conductivity of the composite may be enhanced.
• the average pore size of the pores may be, for example, 0.3 ⁇ m or more, 0.5 ⁇ m or more, or 0.7 ⁇ m or more.
• the "average pore size" according to the present specification means a value that is measured according to a mercury intrusion method.
• a semi-cured product of a heat-curable composition (hereinafter, may be simply referred to as "semi-cured product") means that a curing reaction of a heat-curable composition has proceeded to a certain level or more, as will be described below. Therefore, the semi-cured product of the heat-curable composition may contain a heat-curable resin obtainable by causing raw material components in the heat-curable composition (compounds and the like included in the heat-curable composition) to react, and the like. The semi-cured product may contain compounds and the like of an unreacted portion among the raw material components, in addition to the heat-curable resin.
• the semi-cured product of the heat-curable composition has a structural unit derived from a cyanate group, a structural unit derived from a bismaleimide group, and a structural unit derived from an epoxy group.
• the semi-cured product of the heat-curable composition has a structural unit derived from a cyanate group, a structural unit derived from a bismaleimide group, and a structural unit derived from an epoxy group, production of the composition is made easy, and the adhesiveness of the composite to an adherend may be further enhanced.
• the semi-cured product has a structural unit derived from a cyanate group, a structural unit derived from a bismaleimide group, and a structural unit derived from an epoxy group.
• the semi-cured product contains these structural units to a certain level or more, the dielectric breakdown voltage that will be described below may be further enhanced. Even when the content of the semi-cured product in the composite is small, an excellent dielectric breakdown voltage may be exhibited.
• Examples of the structural unit having a cyanate group include a urethane bond (-NH-CO-).
• Examples of the structural unit derived from a bismaleimide group include a structure represented by the following Formula (1).
• Examples of the structural unit derived from an epoxy group include a structure represented by the following Formula (2).
• These structural units may be detected by using 1 H-NMR and 13 C-NMR. Furthermore, the structural units may also be detected using GPC (gel permeation chromatography). The above-mentioned structural units may be detected by either NMR or GPC.
• R 1 represents a hydrogen atom or another functional group.
• the other functional group may be an alkyl group and the like.
• the semi-cured product may have another structural unit other than the structural unit derived from a cyanate group, the structural unit derived from a bismaleimide group, and the structural unit derived from an epoxy group mentioned above.
• the semi-cured product may contain a heat-curable resin and contains a cyanate resin, a bismaleimide resin, and an epoxy resin.
• the semi-cured product may contain, for example, a phenol resin, a melamine resin, a urea resin, an alkyd resin, and the like, in addition to the heat-curable resin.
• the semi-cured product may contain at least one curing agent selected from the group consisting of a phosphine-based curing agent and an imidazole-based curing agent.
• a phosphine-based curing agent may accelerate a triazine production reaction based on trimerization of a compound having a cyanate group.
• Examples of the phosphine-based curing agent include tetraphenylphosphonium tetra-p-tolylborate.
• An imidazole-based curing agent produces oxazoline and accelerates a curing reaction of a compound having an epoxy group.
• Examples of the imidazole-based curing agent include 1-(1-cyanomethyl)-2-ethyl-4-methyl-1H-imidazole.
• the semi-cured product may be a cured product formed by curing a polymerizable compound (for example, a compound having a cyanate group, a compound having an epoxy group, or the like) included in the
• the curing rate of a heat-curable composition having a curing rate of 100% when the heat-curable composition is in a completely cured state may be adopted as an index.
• the curing rate of the semi-cured product may be, for example, 70% or less, 65% or less, or 60% or less.
• adhesiveness of the composite to an adherend may be enhanced.
• the semi-cured product may embed voids in the resin composite and increase the dielectric breakdown voltage.
• the curing rate of the semi-cured product of the resin may be, for example, 5% or more, 15% or more, 30% or more, or 40% or more.
• the curing rate of the semi-cured product is in the above-described range, the semi-cured product is suppressed from flowing out of the resin composite, and the semi-cured product may be sufficiently retained in the pores of the nitride sintered body.
• the curing rate may be calculated as follows. That is, the curing rate of the semi-cured product impregnated into the nitride sintered body may be determined by the following method. First, the quantity of heat generation Q2 occurring when an uncured heat-curable composition is heated to be completely cured is determined. Then, the quantity of heat generation R2 occurring when a sample collected from the semi-cured product included in the composite is similarly heated to be completely cured is determined. At this time, the mass of the sample used for the measurement by a differential scanning calorimeter is set to be the same as that of the heat-curable composition used for the measurement of the quantity of heat generation Q2.
• the content of the semi-cured product is 20% by volume or more, and may be, for example, 25% by volume or more, 30% by volume or more, 35% by volume or more, or 40% by volume or more, based on the composite.
• the content of the heat-curable composition is 70% by volume or less, and may be, for example, 65% by volume or less, 60% by volume or less, or 55% by volume or less, based on the composite.
• both the adhesiveness and the insulation properties of the composite may be achieved at a higher level.
• the content of the heat-curable composition is in the above-described range, the heat dissipation properties of a laminate obtainable using the composite may be sufficiently suppressed.
• the content of the heat-curable composition is adjusted within the above-mentioned range of 20% to 70% by volume.
• the content of the semi-cured product is obtained by volatilizing the semi-cured product by heating the resin composite at about 600°C and measuring the difference of weights obtained before and after the volatilization.
• the content of the heat-curable composition in the above-mentioned composite may be regarded as the porosity of the nitride sintered body and may be calculated from the following Formula (C).
• the true density of the nitride sintered body is, for example, 2.28 g/cm 3 in the case of boron nitride.
• D means the bulk denisty of the nitride sintered body represented by the following Formula (D).
• Bulk density of nitride sintered body [g/cm 3 ] mass of nitride sintered body/volume of nitride sintered body
• the true density of the nitride sintered body means a value calculated by multiplying the respective true densities of the nitrides by the respective blending ratios (mass ratios).
• the true density of the nitride sintered body is determined by the following Formula (D).
• True density of nitride sintered body [g/cm 3 ] (A ⁇ a + B ⁇ b) ⁇ (a + b)
• the adhesiveness of the composite may be evaluated by using the cohesive fracture area ratio (area%) on the peeling surface at the time of peeling off a sample according to JIS K 6854-1:1999 "Adhesives - Determination of peel strength of bonded assemblies", as an index.
• the cohesive fracture area ratio on the peeling surface of the composite may be adjusted to, for example, 40% by area or more, 50% by area or more, or 60% by area or more, with respect to the total area of the adhering surface of the adherend.
• the dielectric breakdown voltage between adherends after adhesion of the composite is greater than 5 kV and may be set to 5.5 kV or greater or 6 kV or greater.
• the dielectric breakdown voltage between adherends after adhesion of the composite may be, for example, 12 kV or less or 10 kV or less.
• the dielectric breakdown voltage of the composite may be adjusted by means of, for example, the composition of the heat-curable composition, the content of the semi-cured product, and the like.
• the "dielectric breakdown voltage" according to the present specification means a value measured by a withstanding voltage tester (manufactured by KIKUSUI ELECTRONICS CORPORATION, apparatus name: TOS-8700) according to JIS C2110-1:2016.
• a test specimen prepared by the following technique is used. First, the composite is disposed between two sheets of copper plates, the assembly is heated and pressurized for 5 minutes under the conditions of 200°C and 10 MPa and further heated for 2 hours under the conditions of 200°C and atmospheric pressure to prepare a laminate. Pressure is applied in the direction of lamination of the two sheets of copper plates and the composite. On one surface of the laminate, an etching resist agent is screen-printed so as to have a circular shape having a diameter of 20 mm, and on the other surface of the laminate, the etching resist agent is screen-printed over the entire surface (so-called solid pattern shape).
• the etching resist agent is irradiated with ultraviolet radiation to cure, and resist is formed.
• the copper plate on the side on which a circular-shaped resist has been formed is etched with a cupric chloride solution, and a circular-shaped copper circuit having a diameter of 20 mm is formed on one surface of the laminate.
• the laminate having a circular-shaped copper circuit is used as an object of measurement.
• the thermal resistance after adhesion of the composite may be adjusted to, for example, 0.50 K/W or less, 0.40 K/W or less, 0.37 K/W or less, or 0.35 K/W or less.
• the thermal resistance of the composite may be adjusted by means of, for example, the composition of the heat-curable composition, the content of the semi-cured product, the density of the nitride sintered body, and the like.
• the "thermal resistance" according to the present specification means a value measured by a resin material thermal resistance analyzer (manufactured by Hitachi Technologies and Services, Ltd.) according to ASTM D5470.
• the above-mentioned composite may be produced by, for example, the following production method.
• An embodiment of the method for producing the composite is a method for producing a composite having a nitride sintered body having a porous structure and a semi-cured product of a heat-curable composition impregnated into the nitride sintered body, and the method has impregnating a nitride sintered body having a porous structure with a heat-curable composition (hereinafter, also referred to as impregnation); and heating the heat-curable composition to a heating temperature of 80°C to 130°C to be semi-cured (hereinafter, also referred to as semi-curing).
• a heat-curable composition hereinafter, also referred to as impregnation
• the impregnating is a step of impregnating the heat-curable composition by adjusting the temperature of the heat-curable composition to be higher than the heating temperature for the semi-curing and lower than or equal to (the heating temperature + 20°C).
• the heat-curable composition contains a compound having a cyanate group, a compound having a bismaleimide group, and a compound having an epoxy group; and at least one curing agent selected from the group consisting of a phosphine-based curing agent and an imidazole-based curing agent.
• the nitride sintered body having a porous structure may be a product obtained when primary particles of a nitride are sintered together.
• a commercially available nitride sintered body may be used, or separately, a product prepared by sintering a powder containing a nitride may be used. That is, the method for producing a composite may have sintering a powder containing a nitride (hereinafter, also referred to as nitride powder) to obtain a nitride sintered body having a porous structure.
• a nitride sintered body having a porous structure may be prepared by spheroidizing a slurry including a nitride powder using a spray dryer or the like, further molding the slurry spheroids, and then sintering the slurry spheroids.
• a mold may be used, or a cold isostatic pressing (CIP) method may be used.
• the nitride may contain at least one nitride selected from the group consisting of, for example, boron nitride, aluminum nitride, and silicon nitride, and preferably contains boron nitride.
• boron nitride amorphous boron nitride and hexagonal boron nitride may all be used.
• the thermal conductivity of the nitride may be, for example, 40 W/(m ⁇ K) or greater, 50 W/(m ⁇ K) or greater, or 60 W/(m ⁇ K) or greater.
• the thermal resistance of the resulting composite may be further decreased.
• a sintering aid may be used.
• the sintering aid may be, for example, oxides of rare earth elements, such as yttria oxide, alumina oxide, and magnesium oxide; carbonates of alkali metals, such as lithium carbonate and sodium carbonate; boric acid; and the like.
• the amount of addition of the sintering aid may be, for example, 0.01 parts by mass or more, or 0.1 parts by mass or more, for example, with respect to 100 parts by mass of the sum of the nitride and the sintering aid.
• the amount of addition of the sintering aid may be, for example, 20 parts by mass or less, 15 parts by mass or less, or 10 parts by mass or less, with respect to 100 parts by mass of the sum of the nitride and the sintering aid.
• the amount of addition of the sintering aid is adjusted to be in the above-described range, it becomes easy to adjust the average pore size of the nitride sintered body to the above-mentioned range.
• the sintering temperature for the nitride may be, for example, 1600°C or higher or 1700°C or higher.
• the sintering temperature for the nitride may be, for example, 2200°C or lower or 2000°C or lower.
• the sintering time for the nitride may be, for example, 1 hour or longer and also may be 30 hours or shorter.
• the atmosphere during sintering may be, for example, an inert gas atmosphere of nitrogen, helium, argon, or the like.
• a batch type furnace for example, a batch type furnace, a continuous type furnace, and the like may be used.
• the batch type furnace include a muffle furnace, a tube furnace, and an atmosphere furnace.
• the continuous type furnace include a rotary kiln, a screw conveyor furnace, a tunnel furnace, a belt furnace, a pusher furnace, and a koto-shaped continuous furnace.
• the nitride sintered body may be molded into a desired shape, a desired thickness, and the like by cutting or the like, as necessary before the impregnation.
• a solution including a heat-curable composition is prepared in an impregnation apparatus, and a nitride sintered body is immersed in the solution to impregnate the heat-curable composition into the pores of the nitride sintered body.
• the solution including the heat-curable composition may also include a solvent in addition to the heat-curable composition or may include only the heat-curable composition.
• the solvent include an aliphatic alcohol, an ether alcohol, a glycol ether, a ketone, and a hydrocarbon.
• the heat-curable composition contains at least one compound selected from the group consisting of a compound having a cyanate group, a compound having a bismaleimide group, and a compound having an epoxy group, and at least one curing agent selected from the group consisting of a phosphine-based curing agent and an imidazole-based curing agent.
• Examples of the compound having a cyanate group include dimethylmethylenebis(1,4-phenylene)biscyanate and bis(4-cyanatophenyl)methane.
• Dimethylmethylenebis(1,4-phenylene)biscyanate may be commercially purchased as, for example, TACN (manufactured by MITSUBISHI GAS CHEMICAL COMPANY, INC., trade name).
• Examples of the compound having a bismaleimide group include N,N'-[(1-methylethylidene)bis[(p-phenylene)oxy(p-phenylene)]]bismaleim ide and 4,4'-diphenylmethanebismaleimide.
• N,N'-[(1-methylethylidene)bis[(p-phenylene)oxy(p-phenylene)]]bismale imide may be commercially purchased as, for example, BMI-80 (manufactured by K.I Chemical Industry Co., Ltd., trade name).
• Examples of the compound having an epoxy group include 1,6-bis(2,3-epoxypropan-1-yloxy)naphthalene and a compound represented by the following General Formula (3).
• the value of n is not particularly limited but may be set to an integer of 0 or 1 or greater, and n is usually 1 to 10, and preferably 2 to 5.
• 1,6-Bis(2,3-epoxypropan-1-yloxy)naphthalene may be commercially purchased as, for example, HP-4032D (manufactured by DIC Corp., trade name).
• the total amount of the compound having a cyanate group, the compound having a bismaleimide group, and the compound having an epoxy group may be 50% by mass or more, may be 70% by mass or more, may be 80% by mass or more, and may be 90% by mass or more, based on the total amount of the heat-curable composition.
• the content of the compound having a cyanate group in the heat-curable composition may be, for example, 50 parts by mass or more, 60 parts by mass or more, or 70 parts by mass or more, with respect to 100 parts by mass of the total amount of the compound having a cyanate group and the compound having a bismaleimide group.
• the content of the compound having a cyanate group in the heat-curable composition is in the above-described range, the curing reaction at the time of adhering the resulting composite to an adherend proceeds rapidly, and the composite has superior dielectric breakdown voltage after adhesion to an adherend.
• the conditions for adhesion to an adherend are set the adhesion conditions in Examples, the effect of enhancing the dielectric breakdown voltage may be made more notable.
• the content of the compound having a bismaleimide group in the heat-curable composition may be, for example, 15 parts by mass or more, 20 parts by mass or more, or 25 parts by mass or more, with respect to 100 parts by mass of the total amount of the compound having a cyanate group and the compound having a bismaleimide group.
• the content of the compound having a bismaleimide group in the heat-curable composition is in the above-described range, the water absorption rate of the semi-cured product is decreased, and the reliability of a manufactured product may be enhanced.
• the content of the compound having an epoxy group in the heat-curable composition may be, for example, 10 parts by mass or more, 20 parts by mass or more, or 30 parts by mass or more, with respect to 100 parts by mass of the total amount of the compound having a cyanate group and the compound having a bismaleimide group.
• the content of the compound having an epoxy group in the heat-curable composition may be, for example, 70 parts by mass or less or 60 parts by mass or less, with respect to 100 parts by mass of the total amount of the compound having a cyanate group and the compound having a bismaleimide group.
• the content of the compound having an epoxy group in the heat-curable composition is in the above-described range, the decrease in the heat-curing initiation temperature of the heat-curable composition may be suppressed, and it becomes easier to impregnate the nitride sintered body with the heat-curable composition.
• the curing agent may contain a phosphine-based curing agent and an imidazole-based curing agent.
• a phosphine-based curing agent may accelerate a triazine production reaction based on trimerization of a compound having a cyanate group or a cyanate resin.
• the phosphine-based curing agent include tetraphenylphosphonium tetra-p-tolylborate and tetraphenylphosphonium tetraphenylborate.
• Tetraphenylphosphonium tetra-p-tolylborate may be commercially purchased as, for example, TPP-MK (manufactured by HOKKO CHEMICAL INDUSTRY CO., LTD., trade name).
• An imidazole-based curing agent produces oxazoline and accelerates a curing reaction of a compound having an epoxy group or an epoxy resin.
• Examples of the imidazole-based curing agent include 1-(1-cyanomethyl)-2-ethyl-4-methyl-1H-imidazole and 2-ethyl-4-methylimidazole.
• 1-(1-Cyanomethyl)-2-ethyl-4-methyl-1H-imidazole may be commercially purchased as, for example, 2E4MZ-CN (manufactured by SHIKOKU CHEMICALS CORPORATION, trade name).
• the content of the phosphine-based curing agent may be, for example, 5 parts by mass or less, 4 parts by mass or less, or 3 parts by mass or less, with respect to 100 parts by mass of the total amount of the compound having a cyanate group, the compound having a bismaleimide group, and the compound having an epoxy group.
• the content of the phosphine-based curing agent may be, for example, 0.1 parts by mass or more or 0.5 parts by mass or more with respect to 100 parts by mass of the total amount of the compound having a cyanate group, the compound having a bismaleimide group, and the compound having an epoxy group.
• the content of the imidazole-based curing agent may be, for example, 0.1 parts by mass or less, 0.05 parts by mass or less, or 0.03 parts by mass or less, with respect to 100 parts by mass of the total amount of the compound having a cyanate group, the compound having a bismaleimide group, and the compound having an epoxy group.
• the content of the imidazole-based curing agent may be, for example, 0.001 parts by mass or more or 0.005 parts by mass or more with respect to 100 parts by mass of the total amount of the compound having a cyanate group, the compound having a bismaleimide group, and the compound having an epoxy group.
• the heat-curable composition may include other components other than the compound having a cyanate group, the compound having a bismaleimide group, the compound having an epoxy group, and the curing agent.
• other resins such as a phenol resin, a melamine resin, a urea resin, and an alkyd resin; a silane coupling agent, a leveling agent, an anti-foaming agent, a surface adjusting agent, and a wetting dispersant may be further included.
• the content of these other components may be 20% by mass or less, may be 10% by mass or less, or may be 5% by mass or less, based on the total amount of the heat-curable composition.
• the viscosity at 100°C of the solution including the above-mentioned heat-curable composition may be 50 mPa ⁇ second or less, 30 mPa ⁇ second or less, 20 mPa ⁇ second or less, 10 mPa ⁇ second or less, or 5 mPa ⁇ second.
• the viscosity at 150°C of the solution may be in the above-described range, preparation of the composite becomes easier.
• the viscosity at 100°C of the solution may be 3 mPa ⁇ second or greater.
• the viscosity at 100°C of the solution is preferably maintained to be 50 mPa.second or less for 5 hours or more in a state in which the temperature of the solution is maintained at 100°C.
• the viscosity at 100°C of the solution means a value measured using a rotary viscometer under the conditions of a shear rate of 10 (1/second).
• the impregnation may be either under reduced pressure conditions or under pressurized conditions, or the impregnation may be carried out by combining impregnation under reduced pressure conditions and impregnation under pressurized conditions.
• the pressure inside the impregnation apparatus in the case of performing the impregnation under reduced pressure conditions may be, for example, 1000 Pa or less, 500 Pa or less, 100 Pa or less, 50 Pa or less, or 20 Pa or less.
• the pressure inside the impregnation apparatus in the case of performing the impregnation under pressurized conditions may be, for example, 1 MPa or greater, 3 MPa or greater, 10 MPa or greater, or 30 MPa or greater.
• a solution including a heat-curable composition is heated.
• the temperature for heating the solution exceeds the heating temperature for semi-curing.
• the upper limit of the temperature for heating the solution is a temperature lower than or equal to (the heating temperature for semi-curing + 20°C).
• a state in which the nitride sintered body is immersed in the solution including the heat-curable composition is maintained only for a predetermined time.
• This predetermined time may be, for example, 5 hours or longer, 10 hours or longer, 100 hours, or 150 hours or longer.
• the semi-curing is heating the heat-curable composition impregnated into the nitride sintered body to semi-cure the heat-curable composition. Through the semi-curing, the semi-cured state of the heat-curable composition in the composite may be adjusted. The heating temperature at this time is 80°C to 130°C.
• the semi-cured product obtainable by the semi-curing may contain at least one heat-curable resin comprising a cyanate resin, a bismaleimide resin, and an epoxy resin, and a curing agent.
• the semi-cured product may also contain, for example, other resins such as a phenol resin, a melamine resin, a urea resin, and an alkyd resin; and components derived from a silane coupling agent, a leveling agent, an anti-foaming agent, a surface adjusting agent, a wetting dispersant, and the like, in addition to the above-mentioned heat-curable resin and the curing agent.
• the total content of the other resins and the components may be 20% by mass or less, may be 10% by mass or less, or may be 5% by mass or less, based on the total amount of the semi-cured product.
• the impregnation and the semi-curing have been described as separate steps.
• the two do not necessarily have to be steps that are distinguishable from each other, as long as the desired actions of each step are provided. That is, in the middle of the impregnation, the heat-curable composition impregnated into the nitride sintered body may be semi-cured by adjusting the heating conditions. From the viewpoint of sufficiently impregnating the heat-curable composition into the nitride sintered body, it is preferable to provide the impregnation and the semi-curing separately.
• the above-mentioned composite may be used, for example, for the production of a laminate such as a heat-conductive adhesive sheet.
• An embodiment of the laminate includes, for example, a first metal base material, an interlayer, and a second metal base material in this order. The first metal base material and the second metal base material are adhered by the interlayer, and the interlayer is a cured product of the above-mentioned composite.
• the first metal base material and the second metal base material may be metal base materials that are identical to each other or may be different metal base materials.
• the first metal base material and the second metal base material may be, for example, copper, aluminum, or the like.
• the thicknesses of the first metal base material and the second metal base material may be each independently, for example, 0.035 mm or more, or 10 mm or less.
• the first metal base material and the second metal base material may form, for example, a circuit.
• the above-mentioned laminate may be produced by, for example, the following method.
• An embodiment of the method for producing a laminate is a method for producing a laminate including a first metal base material, an interlayer, and a second metal base material in this order, and has disposing the first metal base material, the above-mentioned composite, and the second metal base material in this order, heating and pressurizing the assembly to cure the composite, and forming the interlayer.
• the first metal base material and the second metal base material may be adhered in a short time period.
• the adhesion time may be adjusted to 2 hours or shorter, 1 hour or shorter, or 0.5 hours or shorter.
• the adhesion time required for the adhesion of a metal circuit and metal fins for heat dissipation may be shortened by selecting a composite whose dielectric breakdown voltage obtainable when cured under specific conditions is greater than 5 kV.
• the composite of the present disclosure is implemented using a specific heat-curable composition, production of the composite becomes easier, and also, the adhesion time to an adherend may be shortened.
• the curing time at the time of bringing the resulting composite to stage C may be shortened.
• the mixed powder was charged into a mold and press-molded at a pressure of 5 MPa, and a molded body was obtained.
• the molded body was compressed by applying a pressure of 20 to 100 MPa using a cold isostatic pressing (CIP) apparatus (manufactured by Kobe Steel, Ltd., trade name: ADW800).
• CIP cold isostatic pressing
• the compressed molded body was sintered by maintaining the molded body at 2000°C for 10 hours using a batch type high-frequency furnace (manufactured by Fuji Dempa Kogyo Co., Ltd., trade name: FTH-300-1H), and thereby a nitride sintered body was prepared.
• calcination was carried out by adjusting the inside of the furnace to a nitrogen atmosphere while causing nitrogen to flow into the furnace in a standard state at a flow rate of 10 L/min.
• 80 parts by mass of a compound having a cyanate group, 20 parts by mass of a compound having a bismaleimide group, and 50 parts by mass of a compound having an epoxy group were measured into a container, 1 part by mass of a phosphine-based curing agent and 0.01 parts by mass of an imidazole-based curing agent were added to 100 parts by mass of the total amount of the three kinds of compounds, and the mixture was mixed. Meanwhile, since the epoxy resin was in a solid state at room temperature, the mixture was mixed in a stated of being heated to about 80°C. The viscosity at 100°C of the resulting heat-curable composition was 10 mPa ⁇ second.
• the nitride sintered body prepared as described above was impregnated with the heat-curable composition prepared as described above, by the following method.
• the interior of the apparatus was purged for 10 minutes under the conditions of temperature: 100°C and pressure: 15 Pa.
• the nitride sintered body was immersed in the heat-curable composition for 40 minutes while being maintained under the same conditions, and the heat-curable composition was impregnated into the nitride sintered body.
• the container containing the nitride sintered body and the heat-curable composition was taken out and was placed in a pressure heating impregnation apparatus (manufactured by KYOSIN ENGINEERING CORPORATION, trade name: HP-4030AA-H45), the container was maintained for 120 minutes under the conditions of temperature: 130°C and pressure: 3.5 MPa, and thus the heat-curable composition was further impregnated into the nitride sintered body.
• the nitride sintered body was taken out from the apparatus and was heated for 8 hours under the conditions of temperature: 120°C and atmospheric pressure, the heat-curable composition was semi-cured to prepare a composite.
• the content of the semi-cured product was 25% to 68% by volume.
• the composite obtained as described above was prepared into a laminate, which was obtained by disposing the composite between two sheets of copper plates, heating and pressurizing the assembly for 5 minutes under the conditions of 200°C and 10 MPa, and further heating the assembly for 2 hours under the conditions of 200°C and atmospheric pressure.
• an etching resist agent was screen-printed so as to have a circular shape having a diameter of 20 mm, and on the other surface of the laminate, the etching resist agent was screen-printed over the entire surface. After printing, the etching resist agent was irradiated with ultraviolet radiation to cure, and resist was formed.
• the copper plate on the side on which a circular-shaped resist had been formed was etched with a cupric chloride solution, and a circular-shaped copper circuit having a diameter of 20 mm was formed on one surface of the laminate.
• the laminate on which a circular-shaped copper circuit was formed was obtained, which was an object of measurement.
• the dielectric breakdown voltage was measured for the laminate thus obtained, using a withstanding voltage tester (manufactured by KIKUSUI ELECTRONICS CORPORATION, apparatus name: TOS-8700) according to JIS C2110-1:2016. From the measurement results, the insulation properties were evaluated according to the following criteria. The results are shown in Table 1.
• the composite obtained as described above was prepared into a laminate, which was obtained by disposing the composite between two sheets of copper plates, heating and pressurizing the assembly for 5 minutes under the conditions of 200°C and 10 MPa, and further heating for 2 hours under the conditions of 200°C and atmospheric pressure, and this laminate was used as an object of measurement.
• a 90° peeling test was performed according to JIS K 6854-1:1999, "Adhesives - Determination of peel strength of bonded assemblies", and the area of a cohesive fracture portion was measured. From the measurement results, adhesiveness was evaluated according to the following criteria. The results are shown in Table 1.
• the composite obtained as described above was prepared into a laminate, which was obtained by disposing the composite between two sheets of copper plates, heating and pressurizing the assembly for 5 minutes under the conditions of 200°C and 10 MPa, and further heating the assembly for 2 hours under the conditions of 200°C and atmospheric pressure, and this was used as an object of measurement.
• Thermal resistance was measured according to ASTM-D5470. From the measurement results, heat dissipation properties were evaluated according to the following criteria. The results are shown in Table 1.
• Composites were prepared in the same manner as in Example 1, except that the types and blending ratios of the compound having a specific functional group and the curing agent, and the content of the semi-cured product were changed as shown in Table 1, and evaluation of the dielectric breakdown voltage, insulation properties, 90° peelability, adhesiveness, thermal resistance, and heat dissipation properties was carried out. Examples 2 to 4 and Comparative Examples 1 to 3 are provided for illustrative purposes.
• a composite having excellent adhesiveness to an adherend and excellent insulation properties after adhesion to the adherend, and a method for producing the composite may be provided.

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